Life-course theories expect imprisonment to negatively influence a person’s employment prospects. Incarceration not only instantaneously interrupts a number of life-course domains but may also reduce future opportunities to reconnect to them. This article analyzes the effects of incarceration on employment by using observational data on the employment careers from age 23 up to age 32 in 270 high-risk males. All men had been treated for delinquency and problematic behavior in a juvenile justice institution in the Netherlands. First, we investigate whether specific employment trajectories can be distinguished within the overall employment pattern in this sample. Second, controlling for selection into both incarceration and low-employment participation, we investigate the effect of incarceration on future employment over and above the effect of being convicted.